THEN:

Emily Gould was an assistant editor at Hyperion Books when she appeared in our July 2005 cover story, Smartest Money Moves at Any Age. At 23, she was thriving in her first post-college job, but she acknowledged being less than savvy about money, including failing to take full advantage of her 401(k). “I’d rather be a young person with beautiful shoes than an old person with a roof over my head,” she said then.

NOW:

Part of an early generation of bloggers, Gould left Hyperion in 2006 for a job at Gawker, the media/gossip blogging site. She later wrote about that experience, and her willingness to share personal details online about her life and relationships, in a first-person account for The New York Times Magazine. The story featured a provocative photo of Gould on the cover and generated a torrent of comments, most of them negative. She was stunned by the reaction, but the attention paved the way for a book deal (a memoir later published as And the Heart Says Whatever), for which she received a $200,000 advance.

Gould looks back on the rest of her twenties as “rocky and tumultuous.” The book, published in 2010, sold poorly, and within a few years the money was gone, partly to cover taxes, health insurance premiums and her agent’s commission but also to pay for pricey clothes and an apartment she couldn’t afford. Gould even cashed out her 401(k) retirement account (incurring a big tax bill and a 10% early-withdrawal penalty). “The Emily Gould–specific financial crisis coincided with the global financial crisis,” she says.

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Life in her thirties has been much smoother, says Gould, now 33. Her first novel, Friendship, hit bookstores in 2014 and has earned back its $30,000 advance. Last year, she married writer Keith Gessen; in June, the couple had their first child, Raphael. “These were things I’d always imagined would happen, but it was unclear if they ever would or when,” she says.

Gould is writing another novel, and she co-owns (with Ruth Curry) Emily Books, an online bookstore that offers monthly subscriptions to feminist e-books. Earlier this year, Gould and Curry raised more than $40,000 through Kickstarter to develop the site and partner with Coffee House Press to publish original books.

Any regrets? The way she spent the $200,000 is a big one. “I wish I could go back to that old self and scream, ‘Buy an apartment!’ ” says Gould, who lives with Gessen and Raphael in a rental apartment in Brooklyn, N.Y. Still, “having a child really makes all the other stuff you were anxious about feel like small potatoes.”